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Mn- and Co-Catalyzed Aminocyclizations of Unsaturated Hydrazones Providing a Broad Range of Functionalized Pyrazolines

2021; American Chemical Society; Volume: 1; Issue: 7 Linguagem: Inglês

10.1021/jacsau.1c00176

2691-3704

Moritz Balkenhohl, Sebastian Kölbl, Tony Georgiev, Erick M. Carreira,

Sulfur-Based Synthesis Techniques

Manganese- and cobalt-catalyzed aminocyclization reactions of unsaturated hydrazones are reported. Whereas manganese catalysis provides access to pyrazoline and tetrahydropyridazine alcohols, cobalt catalysis for the first time paves the way for the selective formation of pyrazoline aldehydes. Furthermore, various functional groups including hydroperoxide, thiol derivatives, iodide, and bicyclopentane may be introduced via manganese-catalyzed ring-forming aminofunctionalization. A progesterone receptor antagonist was prepared using the aminocyclization protocol.